Methylamine → (S)-(+)-Mandelamide

Reaction equation

C[NH2:2].[C:3]([O:13]C)(=O)[C@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5]>>[C:3]([NH2:2])(=[O:13])[C@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5]

Participants

Reactant 2

HCID 6329Methylamine

HCID 643570methyl (2S)-2-hydroxy-2-phenylacetate

Product 1

HCID 818990(S)-(+)-Mandelamide

Procedure

To a solution of methylamine (40% in water, 3.8 equivalents) is added, at ambient temperature, methyl (S)-mandelate (1.0 equivalent; commercially available), while keeping the temperature below 30° C. and stirred at ambient temperature until full conversion is achieved. Excess methylamine is removed by azeotropic distillation. Alternatively, after neutralisation with aqueous hydrochloric acid the aqueous solution is saturated with sodium chloride and extracted several times with dichloromethane. The organic layers are combined and the water is removed by azeotropic distillation.

Workup

customthe temperature below 30° C.
customExcess methylamine is removed by azeotropic distillation
extractionextracted several times with dichloromethane
customthe water is removed by azeotropic distillation

Sources & evidence

ORD record: ord-6cc76b3a6a9943eca6dc37b5e07b6955
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247560B2

Reaction notes

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